Theoretical studies of stereoselectivities in the direct anti-Mannich and syn-aldol reactions catalyzed by axially chiral amino sulfonamide
摘要：
The origins of the stereoselectivities in the axially chiral amino sulfonamide-catalyzed direct anti-Mannich and syn-aldol reactions have been studied with the aid of density functional theory method. Transition states of the stereochemistry-determining C–C bond-forming step with the enamine intermediate addition to the imine or aldehyde for the subject Mannich and aldol reactions are reported. BH and HLYP/6-31G** calculations provide a good explanation for the diastereoselectivities in the chiral amino sulfonamide-catalyzed anti-Mannich and syn-aldol reactions. Calculated and observed diastereomeric ratio and enantiomeric excess values are in good agreement.
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DOI：
10.1016/j.molcata.2009.08.026
被引量：
年份：
2009
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